Ever since 1998, when I flipped for Don Roos’ brilliantly sardonic directorial debut, The Opposite of Sex, I’ve been dying to see how he would top it. In 2002 he wrote and directed another film, Bounce, starring Ben Affleck and Gwyneth Paltrow, but it was a bit of a dud. Despite some strong performances and Roos’ sharp, witty dialogue, ultimately the film was a rich set-up that he never quite brought home. Happy Endings is the true successor to Opposite, with an even richer cast of hopelessly, hilariously screwed-up characters and the same sense of surprise — the plot twists are as unpredictable as the characters themselves.

The film navigates the intersections between the lives of 10 characters in contemporary Los Angeles. Some are old friends or lovers, others are related by blood or marriage, and some just slam into each others’ lives, scattering a lot of debris around. There are surface similarities to Paul Haggis’ Crash — the two films are set in the same time and place and have a similarly convoluted structure — but Roos has made the anti-Crash, a film free of moralizing and leaden didacticism. He’s after a looser, more subtle exploration of human nature, one whose results aren’t all predetermined and reduced to a single social factor. He’s trying to understand the consequence of keeping secrets and the ways in which secrets tear people apart or bring them together. His characters are flawed people; they’re liars and withholders, and in their battles to hide the truth they may swing from devious and manipulative to weak and vulnerable in an instant. They have the complications that real people have, and like real people, they rarely conform to our expectations.

Happy Endings bears similarities also to Woody Allen movies like Manhattan and Hannah and Her Sisters and to David O. Russell’s Flirting with Disaster and I ♥ Huckabees, but Roos has a warmer, more empathetic vision than Allen or Russell; his characters are dangerous to themselves and to each other, but even when they know they’re doing the wrong thing they’re never malicious, just frightened, angry, and self-protective. They hurt each other because they just can’t figure out how to behave differently. A prime example: Maggie Gyllenhaal plays Jude, a character with more than a passing resemblance to Christina Ricci’s Dede Truitt in The Opposite of Sex. She’s a savvy manipulator who uses her innocent-little-girl face and firm young body to get what she wants, but where Dede was only a little more than a stock character — the grasping, amoral gold-digger — enlivened by Roos’ dialogue and Ricci’s vamping, Jude is richer and more mysterious. She doesn’t fully understand her own motivations, and at a point in which she’s about to level her most devastating weapon on a guileless patsy, she pulls back, unable to go through with it.

Roos gets a persuasive, subtle performance out of Gyllenhaal, but that’s nothing new for her. What’s more impressive is the way he draws moving, richly felt performances out of actors one might be tempted to dismiss out of hand. I never thought I’d describe a Tom Arnold performance as delicately nuanced, but that’s just what his work here is. Arnold plays Frank, a wealthy widower who’s terrified that his 22-year-old son is secretly gay. Frank is an inarticulate man-child, a guy who can’t figure out how to deal with his son or to romance a woman; he’s had great success in business but his personal life is a series of missed connections and stammered protestations. His son Otis (Jason Ritter) is perhaps an even worse case; he’s so repressed and laden with anxiety that he lacks even the ability to connect with his own feelings. Lisa Kudrow, an alumna of The Opposite of Sex, where she did perhaps her finest work to date, is the film’s central character, Mamie, who is haunted by unanswered questions about her teenaged pregnancy 19 years earlier. When she meets an intense young wannabe-filmmaker (Jesse Bradford) who promises answers to those questions, she’s not sure whether she should agree to his ridiculous terms or call the cops. When she asks her secret boyfriend, a Mexican masseur named Javier (Bobby Cannavale), for help, she gradually learns that she’s not the only one who’s been hiding something from her past (and yes, the title does connect with his job the way you think it does … sort of). Meanwhile, Mamie’s stepbrother Charley (Steve Coogan) is dealing with his own questions about a pregnancy — he suspects that his boyfriend Gil (David Sutcliffe) is secretly the father of the two-year-old son of his lesbian best friend Pam (Laura Dern). The lengths that the characters go to — both to protect their own secrets and to expose other people’s — may be outrageously comic or terribly moving — sometimes both at the same time — but the cast never drops a note.

Roos is clearly pushing himself and his actors, reaching out into a lot of different directions, and he manages to bring all the elements off with relative success. He incorporates narration in an unusual yet effective way, working in asides that recall Godard or Alfonso Cuarón’s Y tu mamá tambien but that appear not as spoken narration but as white-on-black text on a third of the screen. The device widens the story out, giving the audience background information, a character’s thoughts, or an unessential but telling bit of gossip (“Gil is an architect, sort of. He and Charley have been together five years. They will never have a three-way.”) Roos’ direction is more assured than before, with a looseness and dexterity that brings you right up against the characters and their stories. His cinematographer, J. Clark Mathis, uses a shaky handheld camera and has a casual way of finding his way into a scene that gives the film the immediacy of a documentary. There’s life going on around the edges of Mathis’ camera, as there is in a Robert Altman film, and you get the feeling that the characters are moving through a real, populated world full of other liars and secret-keepers. The sex scenes are funny yet affecting, shot close-in so that you focus on the characters’ faces and see the heat — or lack of heat — between them. They’re erotic, ironic, and sometimes painfully sad.

Those scenes help get at the film’s underlying theme: the value and the fragility of human connections. Within each of his overlapping stories, Roos has characters who keep nearly coming together but refuse to let their guard down and allow it to happen or who do come together but are divided by secrets or lies. This could all get very heavy-handed, but Roos’ approach is less that of a teacher or a preacher than that of an eager student asking, “What happens to us when our secrets are revealed?” Happy Endings offers 10 answers. You pick.

Jeremy C. Fox is the managing editor of Pajiba and a member of the Online Film Critics Society. You may email him at jeremycfox[at]gmail.com.